Hydrazine hydrate (1:1) → HCID 178445973, compound

HRID 255616Notes

Reaction equation

HRID 255616 reaction equation
C([O:8][C:9]([NH:11][C@H:12]([C:24]([NH:26][C@H:27]([C:34]([NH:36][C@@H:37]([CH2:46][CH:47]([CH3:49])[CH3:48])[C@@H:38]([OH:45])[CH2:39][C:40](OCC)=[O:41])=[O:35])[CH2:28][C:29]1[N:33]=[CH:32][NH:31][CH:30]=1)=[O:25])[CH2:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1)=O)C1C=CC=CC=1.[OH2:50].[NH2:51][NH2:52]>CN(C)C=O>[CH2:13]([O:50][C:9]([NH:11][C@H:12]([C:24]([NH:26][C@H:27]([C:34]([NH:36][C@@H:37]([CH2:46][CH:47]([CH3:49])[CH3:48])[C@@H:38]([OH:45])[CH2:39][C:40]([NH:51][NH2:52])=[O:41])=[O:35])[CH2:28][C:29]1[N:33]=[CH:32][NH:31][CH:30]=1)=[O:25])[CH2:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1)=[O:8])[C:14]1[CH:23]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 178471826HCID 178471826, compound

Product 1

HCID 178445973HCID 178445973, compoundYield 170.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

134 mg (0.2 mmole) of ethyl 4(S)-[N-benzyloxycarbonyl-3-(1-naphthyl)-L-alanyl-L-histidyl]amino-3(S)-hydroxy-6-methylheptanoate (prepared as described in Example 1) were dissolved in 2 ml of dimethylformamide, and 100 mg (2 mmole) of hydrazine hydrate were added to the resulting solution, which was then stirred at room temperature for 2 days. The solvent was then removed by distillation under reduced pressure, and water was added to the resulting residue to form a precipitate, which was filtered off. The resulting precipitate was washed thoroughly with water and then dissolved in methanol. The solvent was removed by distillation under reduced pressure. A 1:1 by volume mixture of diethyl acetate and diethyl ether was added to the resulting solid residue, which was then finely pulverized and filtered. There were obtained 112 mg of the title compound as a white powdery solid, melting at 120°-127° C., [α]24 -58.6°. (C=0.5, dimethylformamide).

Workup

  1. customThe solvent was then removed by distillation under reduced pressure, and water
  2. additionwas added to the resulting residue
  3. customto form a precipitate, which
  4. filtrationwas filtered off
  5. washThe resulting precipitate was washed thoroughly with water
  6. dissolutiondissolved in methanol
  7. customThe solvent was removed by distillation under reduced pressure
  8. additionA 1:1 by volume mixture of diethyl acetate and diethyl ether
  9. additionwas added to the resulting solid residue, which
  10. filtrationfiltered

Sources & evidence

ORD record
ord-9a77944e2c304bd5aa05cdd87374d2e5
Source dataset
uspto-grants-1987_10
Patent number
US04698329

Reaction notes

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